Chloroform → HCID 22093133, compound

Temperature

0 °C

A solution of 2.0 M lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene (100 ml) was slowly added dropwise to a solution of N-t-butylmethanesulfonamide (15.1 g) in tetrahydrofuran (100 ml) under nitrogen atmosphere taking about 1 hour at −50 to −20° C. After stirring for 1 hour at 0° C. and cooling to −50° C., (R)-1-methyloxethane (8.51 g) was added dropwise thereto. After stirring for 5 days at room temperature, the solution was extracted with water and ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=½) to obtain crude (R)-N-t-butyl-4-hydroxy-1-pentanesulfonamide (6.6 g) as solid. This solid was dissolved by adding chloroform and concentrated under reduced pressure. The residue thus obtained was crystallized by adding diethyl ether. The crystals were separated by filtration and dried under reduced pressure to obtain (R)-N-t-butyl-4-hydroxy-1-pentanesulfonamide (3.39 g) as white crystals.

1. temperaturecooling to −50° C.
2. addition(R)-1-methyloxethane (8.51 g) was added dropwise
3. stirringAfter stirring for 5 days at room temperature
4. extractionthe solution was extracted with water and ethyl acetate
5. washThe organic layer was washed with water
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=½)
9. customto obtain crude (R)-N-t-butyl-4-hydroxy-1-pentanesulfonamide (6.6 g) as solid
10. dissolutionThis solid was dissolved
11. concentrationconcentrated under reduced pressure
12. customThe residue thus obtained
13. customwas crystallized
14. additionby adding diethyl ether
15. customThe crystals were separated by filtration
16. customdried under reduced pressure

ORD record

ord-4ba8a6c9b6584b01aef9d81b0d2c0826

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06420409B1